


Winchester Escort Services part 2

by omgbubblesomg, troubleseeker



Series: 31 fics in 31 days [19]
Category: Supernatural
Genre: Anal Sex, Bottom Dean, Competitive sex, Cunnilingus, Established Relationship, F/M, Kinktober 2017, M/M, Prostitute Dean, Prostitute Sam, Prostitution, Rimming, Spit As Lube, Top Sam
Language: English
Status: Completed
Published: 2017-10-19
Updated: 2017-10-19
Packaged: 2019-01-19 18:08:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,765
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12415251
Author URL: https://archiveofourown.org/users/omgbubblesomg/pseuds/omgbubblesomg, https://archiveofourown.org/users/troubleseeker/pseuds/troubleseeker
Summary: “I wanna see them fuck each other,” the bride stage whispered.Dean caught the corner of Sam’s eye and winked. He extricated himself from beneath a leopard-print dress, just far enough to lick his lips and purr, “We can do that.”





	Winchester Escort Services part 2

**Author's Note:**

> So this is a continuation of an earlier fic, which you can read [here](http://archiveofourown.org/works/12134256). It was written by troubleseeker and I almost exclusively in the comments section (again!) and yes I'm cheating by using a pre-written scene but do you have any idea how hard it is to write a new fic every bloody day? Anyway I wrote a new porny ending for you all so enjoy.  
> I'm posting it as a separate fic instead of a second chapter only for kinktober purposes.
> 
> Kinktober Day 19: **Prostitution/sex work** | olfactophilia | nipple play

“I wanna see them fuck each other,” the bride stage whispered.

Dean caught the corner of Sam’s eye and winked. He extricated himself from beneath a leopard-print dress, just far enough to lick his lips and purr, “We can do that.”

The room was full of sated women, in various stages of undress. They were draped across the furniture as though a hurricane had come through, not two male escorts. But at Dean’s words they looked up as one. Dean could almost see their ears pricking.

Sam knew this game too.

“Fine,” he said, smoothing a hand down the trembling thigh of the youngest bridesmaid. “But I’m fucking you this time.”

The bride interrupted, as they knew she would. “Whoever makes their bridesmaid come first wins.” She bit her lip like maybe it was a step too far, but Dean winked at Sam again.

“Deal,” they said in unison.

The room erupted as the ladies—some of whom had been close to falling asleep—were suddenly alive with the possibility. There was some quick, heated arguing over which two would get to receive the fastest orgasms of their life.

“You already came twice, that’s not fair!” “She’s way more sensitive than Chastity!” “You’re just jealous I get to have both of them!”

Sam smiled charmingly at the lady who eventually won one of the coveted spots. Dean smirked at the other. They’d agreed to both eat out a bridesmaid they hadn’t yet had a go at, for the sake of good sportsmanship. This battle would be won fair and square as far as the drunken ladies were concerned. They didn’t know that Sam was going to win regardless.

In situations like these, unless the crowd had a firm favourite as bottom, they switched equally. And tonight it would be Dean’s turn. Dean had gotten to pound Sam on top of a free bar at some bigwig party last month, while handsy executives took sloppy bodyshots off him. Ergo, it was his turn to take one for the team.

It’d make for a better show anyway. Sam had taken the vanilla lube with him when he ran for the cab, so Dean hadn’t even stretched yet. Watching Sam finger him open would send the crowd even wilder. Champagne and dollar bills had been flowing freely so far, and the finale would end the night with, quite literally, a _bang._ The ladies were already getting worked up, separating into teams based on which brother they were rooting for.

“Someone count down from three,” Dean growled from underneath a sequined miniskirt, hitched high on a redhead’s hips. He’d gotten comfortable on the thick carpet (which would be a bitch to clean after this), with his arms circled under and around the woman’s legs to pet at her stomach.

Sam pulled his girl into position too, and she giggled nervously. “Hey gorgeous,” he whispered up at her. “Must be my lucky day. Can’t wait to make you feel good.” She blushed at his words, relaxing into him and Dean bit back a cheeky remark about Sam getting a head start. 

“Three!” called the bride, shutting the crowd up as they turned to watch the show. “Two!” Everyone else took up the chant so “One!” was loud enough to wake the neighbours.

Sam dove into the gasping woman—Chastity really was a perfect name—sliding a finger in about halfway and sucking her clit. Dean had given him a quick covert signal that told him she was susceptible to g-spot stimulation. She keened pretty much instantly, going rigid at the onslaught of attention.

Sam glanced sideways at Dean, who was taking care to put on a show while attempting to keep a hold of the squirming woman. Her hair colour might have been fake, but her moans certainly weren’t.

It took Sam less than three minutes before Chastity’s legs clamped down around his head and she whimpered out her pleasure. He took his time easing her down from the sudden high with soft passing licks and kisses, finger pumping gently in and out to draw out her pleasure.

Next to him, Dean upped the ante, seeing that Sam had finished. The redhead clawed at his head and literally screamed as he pushed her over the edge.

Sam’s cheer squad were squealing enthusiastically, high-fiving each other as they passed yet another bottle of pink champagne around.

“I won, big brother.”

Dean emerged from between sequin-framed thighs, with most of his lower face slick and shiny. He licked his lips, grinning. “Well,” he said. “You did learn from the best.”

Sam chuckled and pushed against his shoulder, guiding him firmly onto his back, right in the centre of the crowd. People jostled each other to get a good position, some of them aiming for a side-on view, while others stood at Sam’s back, hoping to see some of the—Dean smirked— _main event._

“Where are my pants?” he called. “Beatrice, babe, do you still have them? There’s lube in the back pocket.”

“Don’t bother,” Sam said. “We won’t need it.” He settled between Dean’s parted legs, and Dean groaned, which wasn’t part of the show at all. Getting Sam’s face so close to his cock was one of his favourite things in the world, and it was a simple Pavlovian response that had his dick twitching up, eagerly searching for Sam’s mouth. And if Sam didn’t plan on using lube then that meant he wanted to slick Dean up using just his spit. _Hell_ yeah. Sam probably needed the time to recuperate after their long night. And if eating Dean out was the best way to get them both in the mood then Dean would happily oblige.

Sam licked one long wet stripe up the underside of his cock, sucking the head into his mouth for only a second before he shimmied further down, blowing hot air between Dean’s cheeks.

“Fuck!” Dean swore. Not very eloquent but it was hard to think of anything better to respond when he knew his brother was about to stick his tongue in him.

“Manners,” Sam chided, pinching Dean's inner thigh before sliding a finger against his hole. It was a reminder that they weren’t doing this in the comfort of their own room. They had an audience. Since Sam was about to have his mouth occupied, Dean needed to keep his brain in enough order to be able to work the crowd.

He rolled his eyes but complied, starting to beg as Sam licked up against him. “Come on, little brother. Give it to me. You know how I like it.” The ladies tittered. There were half-voiced gasps when he alluded to the idea that he and Sam did this regularly, so he played that up. “Yeah, just like that. God, your tongue is always so hot.” After a minute it wasn’t even an act anymore. He’d always had a dirty mouth but _God,_ Sam’s felt a thousand times dirtier where it was pressed against him, licking up inside him and sliding one, two, three fingers in, spreading enticingly. “Yeah, Christ, that feels so good. Love how you feel inside me, fuck, can’t wait to get the rest of you. God, you’re so big, you sure you’re my little brother?”

Sam pulled his fingers free and sucked a kiss to the side of Dean’s hole, pulling free with a wet sound that had the closest group of ladies gasping. Dean side-eyed Sam’s erection and—oh hell yeah—Sam was definitely ready to go. Hard as nails and blushing red in a way that had Dean biting his lip. He wanted that inside him right fucking now.

“You never shut up when I do that,” Sam said fondly, stroking himself. “What do you reckon, ladies? Think I can get him speechless?”

“Fuck him!” “Do it!” “Oh hell, yes.” “This is so fucking hot.”

Sam slung one of Dean’s legs over his shoulder, and Dean held the other one with a hand beneath his knee so Sam could situate himself comfortably while still giving the room a good view. “Come on,” Dean goaded. “You’ll have to give it to me good if you want to shut me up.”

Sam smirked, and pressed in. Dean arched as much as he could from his position. It didn’t matter how much lube they used or how stretched he was, Sam always felt fucking _enormous,_ and _Christ_ it was one of Dean’s favourite things in the world, feeling the thick heat of it shove up into him. _So_ perfect. Sam knew exactly how to do it. Years of practice had him going just too fast, making Dean gasp at the stretch of it. He didn’t bother trying to hold any of the sounds in. Sometimes when they worked gigs together they were supposed to be background entertainment. Silent and pretty. Tonight was not like that. The women had pushed the tables aside to see better. They were giggling and screaming and touching themselves as if they’d never seen anything like it. Probably they hadn’t.

Sam drove deeper and Dean arched again, moaning and swearing and generally making as much of a scene as he could. It wasn’t difficult, really. Not with Sam working him like this. He hiked Dean’s leg up a little higher to hit his prostate on the next pass, and Dean cried out. He loved this. Nearby, one of the ladies copied his cry, a surprised sound that made him think she had probably reached her own orgasm, far sooner than she had expected.

Yeah. He and Sam made such a team.

His dick was dribbling precome and Sam slid a finger through the mess, transferring it to Dean’s mouth. Dean garbled something blasphemous around the intrusion, sucking Sam clean.

“God, your _mouth,_ De.” Sam thrust hard and Dean moaned unintelligibly. He knew where his brother was going with this. “Come on, ladies. You don’t believe me? You have to try him out for yourselves. See if you can get his tongue to do something more useful than swearing.”

“ _Please,_ ” he begged, scrabbling against the floor with his free hand as though he needed something to hold. Sam angled perfectly inside him to have his dick twitching again and it was far too easy to force a tremble into his voice. “Fuck, _please,_ ” he begged again. And of course no one could deny them for long. Not when Sam was glistening with sweat and body glitter, and Dean was tensed like a bowstring beneath him.

The maid of honour sauntered forward to catcalls and a rain of banknotes.

 

 

**Author's Note:**

> Some of you may have noticed that I changed the series name. This is due to the fact that some of these fics aren’t short, some of them aren’t hot, and some of the aren’t PWPs. Honestly I should just rename the series “31 things I wrote” but anyway. In my brain’s continuing attempt to never let me write anything short ever again, please look forward to tomorrow’s fic, which is getting so long it now has fucking CHAPTERS. Jfc.
> 
> Tune in for Kink Day 20: threesome. 
> 
> ALSO! I am part of the Fandom Loves Puerto Rico charity auction, and I'm auctioning my services as your personal fanfic kink creator! Do you want a sequel for any of these Kinktober fics? Have you been hankering for a particular scene or pairing and really wish someone would write it? Or something else? Go place a bid and if it's the highest then I'll write something for you :) It’s all for a good cause! There's also art, beta services, merch and other fun things, so there's something for everyone!  
> To find my auction page, go here: <https://fandomlovespuertorico.dreamwidth.org/3482.html?thread=295834#cmt295834>


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